81 total properties
Did you mean the neighborhood Winter Park?
View 1235 VIA ESTRELLA Winter Park, FL MLS# O6388913
  • Recently Listed with Virtual Tour
1 of 14
$5,895
4

Beds

3.0

Baths

2,207

Sq.Ft.

1235 VIA ESTRELLA

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 200 SAINT ANDREWS BOULEVARD 2302 Winter Park, FL MLS# O6386317
  • Recently Listed with Virtual Tour
1 of 23
$1,750
2

Beds

2.0

Baths

987

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 2302

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 220 W READING WAY Winter Park, FL MLS# O6389180
  • Recently Listed with Virtual Tour
1 of 37
$5,900
4

Beds

3.0

Baths

2,741

Sq.Ft.

220 W READING WAY

Winter Park, FL

Courtesy of HEWITT RESIDENTIAL, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 7326 SWALLOW RUN 7326 Winter Park, FL MLS# O6389142
  • Recently Listed with Virtual Tour
1 of 7
$1,500
2

Beds

2.0

Baths

800

Sq.Ft.

7326 SWALLOW RUN 7326

Winter Park, FL

Courtesy of NOBSKA REAL ESTATE LLC
View 1802 ARBOR PARK DRIVE Winter Park, FL MLS# O6389650
  • Recently Listed with Virtual Tour
1 of 35
$4,500
4

Beds

3.0

Baths

1,808

Sq.Ft.

1802 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of TBRO REALTY LLC
View 952 FAIRWAY DRIVE Winter Park, FL MLS# G5109152
$3,300
3

Beds

2.0

Baths

2,007

Sq.Ft.

952 FAIRWAY DRIVE

Winter Park, FL

Courtesy of THE FLORIDA PROPERTY SHOP SALE
View 252 BALFOUR DRIVE Winter Park, FL MLS# O6388475
  • Recently Listed with Virtual Tour
1 of 25
$2,500
3

Beds

2.1

Baths

1,727

Sq.Ft.

252 BALFOUR DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 663 HAROLD AVENUE Winter Park, FL MLS# O6387903
$42,000
10,429

Sq.Ft.

663 HAROLD AVENUE

Winter Park, FL

Courtesy of RCI REAL ESTATE INC.
View 687 HAROLD AVENUE Winter Park, FL MLS# O6387921
  • New Construction
1 of 3
$84,000
4,500

Sq.Ft.

687 HAROLD AVENUE

Winter Park, FL

Courtesy of RCI REAL ESTATE INC.
View 3035 GEORGE MASON AVENUE D19 Winter Park, FL MLS# TB8482802
  • Recently Listed with Virtual Tour
1 of 16
$1,350
Studio

Beds

1.0

Baths

549

Sq.Ft.

3035 GEORGE MASON AVENUE D19

Winter Park, FL

Courtesy of FRIENDS REALTY LLC
View 307 SANDLEWOOD TRAIL Winter Park, FL MLS# O6387188
$1,895
2

Beds

2.1

Baths

960

Sq.Ft.

307 SANDLEWOOD TRAIL

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 527 LANGHOLM DRIVE Winter Park, FL MLS# O6387427
$6,750
4

Beds

3.1

Baths

3,276

Sq.Ft.

527 LANGHOLM DRIVE

Winter Park, FL

Courtesy of WOODRUFF REALTY, INC.
View 4550 PALMETTO AVENUE Winter Park, FL MLS# O6388575
  • Recently Listed with Virtual Tour
1 of 28
$78,750
4,206

Sq.Ft.

4550 PALMETTO AVENUE

Winter Park, FL

Courtesy of SOLANTIS LLC
View 2075 JEWELL AVENUE Winter Park, FL MLS# O6386721
$6,995
5

Beds

4.0

Baths

2,918

Sq.Ft.

2075 JEWELL AVENUE

Winter Park, FL

Courtesy of URBANISTA BROKERS
View 1815 BARKER DRIVE Winter Park, FL MLS# O6386321
$4,000
4

Beds

2.0

Baths

1,548

Sq.Ft.

1815 BARKER DRIVE

Winter Park, FL

Courtesy of SOTERA LIVING
View 151 N ORLANDO AVENUE 118 Winter Park, FL MLS# O6386414
$2,200
3

Beds

2.0

Baths

1,500

Sq.Ft.

151 N ORLANDO AVENUE 118

Winter Park, FL

Courtesy of FLORIDA DREAMS REALTY GRP INC
View 609 MONTEGO BAY COURT 609 Winter Park, FL MLS# S5144764
$1,850
2

Beds

2.0

Baths

1,120

Sq.Ft.

609 MONTEGO BAY COURT 609

Winter Park, FL

Courtesy of JOSE ORLANDO RODRIGUEZ
View 2743 SANBINA STREET Winter Park, FL MLS# O6386314
$2,500
3

Beds

2.0

Baths

1,226

Sq.Ft.

2743 SANBINA STREET

Winter Park, FL

Courtesy of BELMONT REALTY
View 301 W COMSTOCK AVENUE Winter Park, FL MLS# O6385827
  • New Construction with Virtual Tour
1 of 12
$6,000
2

Beds

2.1

Baths

1,500

Sq.Ft.

301 W COMSTOCK AVENUE

Winter Park, FL

Courtesy of THE SYDGAN CORP
View 1850 WHITEHALL DRIVE Winter Park, FL MLS# O6385792
$3,475
3

Beds

2.0

Baths

1,670

Sq.Ft.

1850 WHITEHALL DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES

About Winter Park

Long considered one of the most desirable addresses in Central Florida, Winter Park has been experiencing a wave of new construction along with revitalization of historic areas.  In some instances, developers are choosing to raze older buildings and replace them with luxurious new homes, some that surpass the $1 million price range.  Handsome new residential villages can include exceptional amenities like lakefront parks, pools, and nature preserves.  Winter Park offers a number of amenities that are unusual for a smaller town, including the Rollins College.  This highly respected, private, liberal arts college with its lush campus enriches the entire community educationally, culturally, and economically.  However, the college is not the town's only point of pride.  One of the world's most comprehensive collections of the works of Louis Comfort Tiffany is permanently housed in the Charles Hosmer Morse Museum of American Art.  Aficionados of shopping are drawn to Park Avenue, a quaint district where an oak-shaded park and bandstand are surrounded by art galleries, museums, clothing stores, retail outlets, and wonderful boutiques.  

Listings in Winter Park, FL

328

Estimated median home price

$762,500
Winter Park FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Park, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Park, FL.

Homes for Sale by Price in Winter Park, FL

PriceCount
$0 - 100K4
$100K - 200K46
$200K - 300K21
$300K - 400K16
$400K - 500K29
$500K - 600K15
$600K - 700K22
$700K - 800K17
$800K - 900K10
$900K - 1M9
$1M - Max139

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family192
Townhouse19
Condo83
Commercial3
Rental86
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 3/24/2026)

Information deemed reliable but not guaranteed.

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 3/26/2026.